


Our Silhouettes Against the Night Sky

by no_regrets_coyote (athenadevice)



Category: Supernatural
Genre: Adultery, Alternate Universe - Human, Alternate Universe - Modern Setting, Alternate Universe - Romantic Comedy, Cas as a dog owner, Cheating, F/M, M/M, Misunderstandings, Sam being a cheating ass
Language: English
Status: Completed
Published: 2013-11-26
Updated: 2013-12-21
Packaged: 2018-01-02 17:51:56
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 17,617
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1059769
Author URL: https://archiveofourown.org/users/athenadevice/pseuds/no_regrets_coyote
Summary: <blockquote class="userstuff">
              <p>Dean Winchester's life is currently a wreck. He's living in an apartment he can't afford, has child support to pay for a daughter he barely sees, and now has to deal with keeping Sam's affair a secret. On top of that, the man involved in the affair with Sam, Castiel Novak, seems to hate Dean and Dean's pretty sure the feeling is mutual. Which doesn't really explain why Castiel keeps wanting to hang out with Dean or why Sam seems to think that it's a good idea for Dean and Cas to be friends. And everything gets just bit more complicated when Dean realizes that maybe he wants to be more than just friends with Cas.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This fic began as the Destiel version of the movie _Manhattan_ , but quickly grew into something else entirely. Because of its origins, the character that Sam is based off of is an asshole and sadly, I must warn you, Sam follows suit in this fic (I love him, I really do).

It was in a crowded booth at the Harvelle Roadhouse Bar that Dean Winchester discovered that his brother was having an affair. 

The Harvelle Roadhouse Bar was the sort of the place where only the blue-collar regulars and drifters-who-would-never-visit-again came. Dean Winchester was the former. From his spot in the bar- the booths being the best seats in the house thanks to him knowing the owner, Ellen, personally- he could see the entirety of place clearly. The smell of smoke, despite the no-smoking laws, hanged heavily in the air, along with the drunken murmurs of travellers and the silence of the regulars.

Tonight, Ellen mans the bar (as always), her eyes drifting across the room before landing where Dean sits with his brother, Sam, and Sam’s wife, Jess. Ellen nods she makes eye contact with Dean, but he can see her tense when she spots her daughter, Jo, sitting with them. Dean has been coming to this bar for a few years, but he still doesn’t get total trust from Ellen who is overprotective of her only child. This was partly based on Dean’s well-earned reputation as a womanizer and along with the fact that Jo had harboured a teenaged crush on Dean when they first met. Jo had gotten over that quickly and they had a teasing, but good, friendship. 

Ellen’s eyes also narrow when she looks at Sam and Dean can’t blame her for that either. Something about Sam is off this evening and it seems so obvious. Dean was certain Jess would notice and would comment on it. For the life of him, Dean couldn’t figure out what was bothering Sam. It couldn’t have been a case because Dean remembered his brother bragging about how relaxing work was at the moment (which was totally unfair as Dean was dealing with a high-stress writer currently and the return of subpar book series). It couldn’t have been Jess, because Jess and Sam were considered the perfect couple- almost nauseatingly so. They were seemingly All-American in how they met during college, and how they married shortly after Sam graduated from law school. They both worked well-paying jobs and were young, intelligent and well adjusted. Hell, Dean hadn’t even seen them fight once. Yet tonight, Sam was nervous and, despite the fact he was leading the conversation, distant. 

“Dude, what’s up?” Dean asks when Jess excuses herself to use the bathroom and Jo had cleared off to finish her shift. 

“Nothing,” Sam mutters, looking at the beer in his hands. Dean rolls his eyes. It was like talking with 15-year old Sammy, the moody emo kid that Dean hoped to never see again. 

“Hey don’t give me that. You’re my brother and I know when something’s wrong with you.” 

If it had been any other night Dean would have received the infamous Sammy bitchface, but tonight Sam just shifts uncomfortable in his seat. 

“Come on, spill.” 

Sam leans forward slightly and lowers his voice. “You promise you won’t tell Jess?” Dean nods. “It’s kind of big, that’s all.” 

“Kind of big like you’re going to be arrested big? Like you lost your job? Did you lose your job? Is that why work has been so light for you?”

“No, Dean, it’s not that. I’ve just met someone,” Sam confesses. 

“Met someone? Met someone like…?”

“Like I’m having an affair,” Sam says and look, there’s that bitchface that Dean knows and hates.

Dean nearly tips over his drink. “You’re having an affair? Another one?”

All right, so the marriage of between Sam and Jess wasn’t perfect. Sam’s high-stressed job had lead to a couple of small affairs on the side. Dean wouldn’t have known about them except that Sam had gotten into a dangerous situation with his last flame, which had resulted in Dean being recruited to pick up the pieces. Dean swore he would keep out of his brother’s love life after that last fiasco, but that still didn’t mean he approved of Sam’s coping methods. 

“So, you’re going to be arrested again?” Dean asks, taking a sip of his beer. “Do I need to bail you out?” 

“See, it’s not just another affair, Dean. I really feel like we have this…” Sam drops eye contact with Dean, instead choosing to play with the straw wrappers on the table. 

“This what?” Dean pushes. He knows where this is going, but he needs it confirmed by Sam himself. 

“This connection,” Sam blurts out. “I think this might be the one. Like I might be seriously in love.”

“The one? I thought Jess was the one? What makes this person so special?” 

“I can’t explain. I mean- they’re not even my type- they're nervous and high-strung.” 

“Sounds like you picked yourself a winner there, Sammy,” Dean scoffs. This is typical of Sam. Sam has this great girl, perfect some might say, and he’s running around with some slut that could lead him to ruins. Jess is the only girl Dean has every approved of and Sam can’t be happy with just her.

“Like I said,” Sam continues with a shrug, “we have this connection. We can talk about anything, anything at all. I’ve never met a person so intelligent.” 

Dean’s disapproval must be all over his face, because Sam just frowns at him and adds defensively, “Anyways, it’s not like you’re in the position to judge, certainly not after your last ex.” 

Which is kind of a low blow. 

The ex that Sam was referring to was Lydia. They started off as a one night stand ( _a really good one night stand_ ), but had agreed to stay together after she found out she was pregnant. It had only lasted two years before she left him to join some lesbian colony (okay, had left him for another woman who just so happened to be part of this weird colony-like thing), taking Emma with her, which had left him to deal with a bruised ego and child support. 

“Hey! I got that aspect of my life under control.”

“No you don’t!” Sam laughs. “Isn’t she writing that book based on her turn to lesbianism thanks to you?”

“Sam, I told you to leave this alone after you couldn’t figure out a way to sue her. Obviously, you need to figure out your own life first.” 

“I can do that on my own, Dean,” Sam snaps back. 

“Yeah, well, just don’t leave your wife without thinking about it.”

“Dean,” Sam warns. “Just leave it alone.” 

They sit in silence, both mad at each other, until Jess returns. 

“Ready boys?” Jess asks, grabbing her coat from the booth. 

“Of course. We were just waiting for you,” Sam says, smiling at her before giving Dean a pointed look. 

-

“Nobody is going to believe that.” 

Dean sits at his desk, papers scattered across his desk, looking at a scruffy nervous writer. The writer in question is one Chuck Shurley, better known by the public as Carver Edlund, the creator of the _Supernatural_ series and Bobby Singer’s (Dean’s boss) best client. He is the one who sells the most books, despite the fact that he hasn’t published a book in nearly three years, and he is the one that Bobby is banking on to bring in the big bucks.

Dean doesn’t see it though. Chuck is small, squirrelly looking, unshaven and shakes like he has the DTs (which Dean suspects might be the case). Chuck looks out of place with his rumpled jeans and stained t-shirt, although it’s a vast improvement from his usual boxer/housecoat combination that Dean usually sees him in when they conference at Chuck’s house. The fact that Chuck has even left his house is considered remarkable, but Dean thinks otherwise. 

“Angels, Chuck? Really?” 

“It needs to be angels, Dean. They’re the only ones with enough power to go through hell and rescue a soul, especially one as broken and torn as-”

“Yeah, but I don’t think readers are going to buy that. They’ve been waiting three years for you to continue writing this series and they’re getting angels. Not only that- angels who are dicks!” 

“I wanted to step away from the notion of angels as guardians with fluffy wings,” Chuck explains. “I wanted them to be badass, alien-like. Far removed from humanity.” 

“Yeah, you did a good job with that!” Dean snaps, pointing to the papers in front of him. “You’ve introduced another race of creatures that no one is going to like.” 

“I don’t know about that,” Chuck mumbles, picking at his jeans. 

“Well I do,” Dean says, tossing the manuscript to Chuck. “I don’t know how I’m going to market it without saying what brings our main character back from hell.”

Chuck looks like he’s about to cry, so Dean calms down. 

“I’ll figure something out,” Dean sighs. “Bobby loves it, and it’s Bobby’s word that’s final. I just don’t know how we’re going to do at the Release Party without mentioning angels, but I’ll swing it somehow.” 

Instantly, the hurt-puppy look is gone from Chuck’s face and Dean can hear him stutter out a ‘thank you’. Dean just shakes him off. Bobby might love the books, but if Dean had any say in the matter those books would have never seen the light of day. 

-

The white light wakes Dean from the light slumber he is in and he rubs his eyes, looking over to see Jo absorbed with the movie. Jo had picked the movie that night and it wasn’t to Dean’s taste (too bad he sucks at Rock, Paper, Scissors). Even if it had been a good movie, Dean wasn’t sure he would have been able to pay attention anyways. His free time is spent worrying about his baby brother and how Sam is currently handling this affair, which is apparently more than just an affair, that he’s having. His brother had confessed to being in love with this girl, which had shaken Dean. Dean had thought Sam and Jess’s marriage was solid, that they were really in love with each other, and that these affairs were just coping methods to deal with stress. The confession that love might be involved meant these affairs were something more to Sam, something deeper. And it also meant to Dean that Sam and Jess’s marriage wasn’t working and that frightened him. If the perfect couple couldn’t stay together, than who could?

“Hey, what’s on your mind?” Jo asks, poking him in the side. 

“Nothing. Don’t worry about it,” he grunts in pain. Jesus, her fingernails were sharp. 

“Is it about Sam?” 

“Like I said, nothing for you to worry about.” 

“Dean,” she states in her tell-me-or-I-tell-my-mom voice. 

“You know Sam’s having an affair right?” Dean confesses because he could never hold his own against the Harvelle women. Jo doesn’t even have the decency to look shocked by this. She just nods.

“It seemed kind of obvious. Is he dating another Ruby?” 

Ruby was the girl that introduced Dean to Sam’s other life. Ruby was pretty, feisty and also evil. She had racked up debt all over town, had several drug possession charges against her, and had a love of cocaine that Sam didn’t mind. Together the two managed to crash Sam’s car and end up in jail with a DUI, which Dean had to bail them out of. With Dean’s urging, Sam broke up with Ruby and they had told Jess that the accident had been caused by someone taking a joyride and all the charges had been dropped against Sam thanks to the fact they were friends with the sheriff. Ruby didn’t take their break-up well and there was some creepy-stalking afterwards that had resulted in Jo being recruited to help the boys deal with her. It had been an interesting and stressful time in their lives and Dean and Sam both owed Jo big time. 

“Don’t think so. Apparently, she works with Sam and she’s high-strung and nervous,” Dean says, taking a sip of his beer.

“Sounds like a keeper,” Jo snorts. 

“That what I said. Anyways, he might be in love with this girl and he’s talking about leaving Jess, like for good.”

“He’s been with her too long, that’s all. He missed out on his slutty college years because of her and now he’s trying to make them up. He’ll get his head out of his ass and he’ll realize that Jess is the girl for him.” 

“You think so?” 

“I guarantee it,” she says, lifting her beer bottle in the air. “Hey, can I say I stayed at your place last Friday? I need an alibi for my mom.” 

“Um… I think that’s a bad idea.” 

Dean could just imagine the torture Ellen would inflict on him if she found out. 

“Come on, you’re not seriously scared of my mom, are you?” 

“Honestly, yes. Yes, I am.” 

“She’s not that scary,” Jo says with a laugh.

“Yeah, well you’ve never had a shot gun pointed at your privates, have you?” 

“She does that to all my male friends,” Jo says with an eye roll. “Besides, I think you’re more worried about losing a good drinking spot,” she teases.

“I’d hate to lose it. You have to hand it to your mom- it is the best spot in town.” 

He probably deserved that last slap to his chest.


	2. Chapter 2

**Summary for the Chapter:**

> In which Westerns face multiple abuse, Castiel gets off on the wrong foot, and Dean shares pie.

Dean couldn’t believe that he was dragged to an art gallery on his day off. Usually his weekends were spent cleaning up his apartment or working on his car, generally nothing as _cultural_ as an art gallery. Yet, here he was with Jo, wasting a Saturday looking at art. Which was fine, except that it was modern art. Art like Monet he got, it was boring, but he got it. Spending the day looking at twisted metal that represented the struggle of man or some crap like that was another matter. If he wanted to look at metal he could spend the day fixing his car, which was right now sitting at a friend’s garage without a carburettor. Sadly, he had made plans to hang out with Jo, and it was her turn to pick and she didn’t want to go to Monster Trucks again. 

The first part had been a bust, but the second part of the exhibit was photographs. This he understood, although in this case, it seemed to be a display of hipster photographs of half of a bike wheel or rain or something. He was looking at bits of something, an incomplete picture, and it was kind of pissing him off.

“Dean!” he hears suddenly, jerking him out of the bored trance he was currently in. He sees his brother rushing towards him, his tall figure causing the crowd to part.

“What are you doing at an art gallery?” Sam scoffs. 

“What? You think I can’t like art?” 

His brother raising an eyebrow at him. 

“Jo forced me,” Dean mumbles, pointing to the blonde who was just a few spaces away from them. 

“I’m glad to see that Jo is a good influence on you for once,” Sam says with a smirk. 

“Um, hem,” coughs someone behind Sam. Out steps a short man. Dean’s eyes are drawn automatically to the man, mostly because he’s wearing a beige trench coat in May, and a really ugly one at that. 

“Oh sorry,” Sam says. “This is Castiel Novak, a friend of mine from work.” 

“Hey,” Dean nods. 

Castiel returns it. “It is a pleasure to meet you, Dean,” he says in a surprisingly low voice- like the sort of voice Dean hears from those phone-sex operators. “Sam had told me a great deal about you.” 

“Funny, he never mentioned you.” 

“Dean! I told you all about him the last time we hung out! Remember at the bar with Jess and Jo.” 

“Oh, so you’re…” Dean looks to Sam, who is blushing slightly. Well this is a game-changer. Not only is his brother in love, he’s in love with a dude. Not that Dean is judging- it’s just that Dean has always been the bi one. “Actually, I have heard of you. It’s nice to finally meet you.” 

They shake hands and Dean takes this chance to take another look at his brother’s lover. He was shorter than Dean with dark hair and bright blue eyes. Despite it being a beautiful Saturday, he was dressed in a suit, which was covered by the aforementioned trench coat. He looked professional, stiff and certainly in Sam’s league, although not someone Dean would guess to be Sam’s type. Certainly, nothing like Jess. 

“Oh Sam,” Jo laughs as she joins the group. “It’s nice to see you here. Not surprised though.” She shakes hands quickly with Castiel. 

“Well, I’ve been hearing good things about the Jones collection, so we just had to see it,” Sam explains. 

“Yeah, it’s been the best part of the gallery,” Dean agrees, thinking he has enough knowledge of it to hold a proper conversation.

“Really, you liked that?” Castiel says dubiously. 

“Yeah?” Dean shifts uncomfortably. Castiel is staring at him and Dean suddenly feels awkward because of this. 

“Oh,” Castiel says raising an eyebrow and drops his gaze with Dean. 

“Did you?” Jo asks, trying to break the tension caused by that exchange. 

“No, it seemed very derivative. Just like Chapman, but with none of the wit.” 

“Well, we didn’t like it as much as we like Palin’s sculptures,” Dean offers, although he has no idea what the sculptures are about. Jo seemed to like it, so he guesses it’s all right. 

“Really? You like the metal sculptures?” Castiel states with a sniff. 

“You didn’t like it?” Castiel shrugs. “It was better than that glass cube thing. That was a piece of junk being oversold as art,” Dean laughs. The rest of the group laugh too, except for Castiel.

“Now that,” Castiel interrupts, “to me was brilliant. Absolutely brilliant. It was textural and it had this negative capability. Everything else in here is bullshit.” 

This, of course, silences everyone else. The room feels too small. 

“Maybe we should go outside,” Sam suggests weakly. 

 

“Castiel used to work with Milton and Crowley in their finance department before he moved firms,” Sam explains. 

The four of them are walking aimlessly down the street. Jo and Sam have taken the outside, which forces Dean into the centre, next to the uncomfortably stiff presence of Castiel Novak, who stands besides him almost as if he is afraid of Dean. Dean isn’t sure what to make of Castiel- he seems quiet, but he’s abrupt to the point of rudeness and he makes the entire conversation feel formal, which is hard for Dean to get around. 

“What do you do?” Castiel asks politely.

“I work at Singer’s Publishers.” 

Castiel nods and looks over to Jo. “How about you?” 

“I’m a student,” she laughs, “but I also work at my mom’s bar.” 

“You’re still in school,” Castiel says with disapproval. “You’re younger than I thought.” As Castiel turns to look at Sam, Dean catches Jo’s eye and she looks like she’s trying to hold in a laugh. 

“I think Jones is overrated,” Sam interrupts. “Actually, I think he might be a candidate for the academy,” he says to Castiel. Castiel lets out a snort of amusement. Dean shoots his brother a questioning look. “Castiel and I have created this academy of the overrated for just deserving people as Carl Jung.” 

“HG Wells, Kurt Vonnegut, and Christopher Nolan,” Castiel adds. 

“Hey, Vonnegut is not overrated!” Dean interjects. Castiel scoffs at that while Sam tries to hide his smirk. “While you’re at it, why don’t you add Steven Spielberg?” Dean snaps. 

“Okay, how about Clint Eastwood or John Ford?” suggests Castiel. At that, Dean clutches his chest with his hand. Castiel has gone too far. 

“Clint Eastwood, overrated? I’m sorry, but you’re just wrong. Eastwood is a legend, man.”

Sam laughs silently next to Castiel. Dean glares at his brother, hoping Sam will defend him. Jo isn’t going to help; Dean can hear her snickering next to him. 

“Dean has what we call a fetish for Westerns,” Sam explains. 

“Really?” Cas says with disbelief, turning to look at Dean. “I thought no one liked Westerns after the age of ten.” 

Dean nearly chokes. Jo bursts out laughing. 

“Sorry what?” 

“They’re just so plot-less. Every movie seems the same. The oversimplification of human nature, putting people into boxes of either good or bad. Indians are always the villains and the white Americans always win in the end. It seems incredible that a man of your age would enjoy such things.” 

Dean stands there stunned for a moment, unable to think of snappy comeback. The only thing he can think of is “oh, well you’re a oversimplification” and that’s just lame. Instead, he clears his throat. “I think we better get going.” 

Castiel looks immediately apologetic. “I’m sorry if I overstepped a line. I don’t really want to have this conversation. It’s just that I’m from Illinois, we believe in God.” 

“What the hell does that mean?” Dean cries out. 

-

“What a creep,” Dean says angrily to Jo as they enter the Roadhouse for her next shift. “Could you believe him?”

“He seemed a bit nervous,” Jo suggests weakly, although there’s still a smirk on her face. 

“Where does he get off dissing Westerns?” Dean rages as Jo passes out coasters. “Also, where were you guys when he was abusing Eastwood. You both love him.” 

“I don’t know why you’re getting so mad,” Jo shrugs. 

‘I’m mad because I don’t like that pseudo-intellectual type like Sam seems to. I mean to not like Eastwood! But Sam has always been a sucker for those types.” 

“I have a feeling that Sam really likes him,” Jo suggests softly. 

“That will never cease to amaze me,” Dean scoffs. 

-

“I just don’t get it,” Dean mutters. He is sitting at Sam’s kitchen table, rummaging through last month’s collection of bills. Sam sits next to him with a beer in hand and silent, although Dean is certain that Sam is secretly laughing at him. “Where did the money go?” he said, throwing his hands up in the air. 

Dean knew that lately his budget was getting tight, what with child support and the expenses he needed to fix his car, but he thought he had enough to not be living on beans for the next month. 

“Maybe, you spent it on booze,” Sam suggests and Dean certain he can sense smugness in the tone. Sam has always disapproved of Dean’s drinking habit, but the brothers had an unspoken agreement that if Dean left Sam’s love life alone (and his hair length), Sam would leave Dean’s love of alcohol alone. Dean ignores his brother remark, and continues shuffling through the bills. 

“So what are you going to do for cash?” Sam asks carefully. “I mean this hasn’t been the first time you’ve been short, Dean. I could… I could lend you some.” 

“I can handle it, Sam. It’s fine.” 

“Seriously, if you need help, I can always lend you a couple of bucks.” 

“No! I’ll just have to cut back on what I send to Dad and I’ll talk with Lydia about next month’s payment.” 

Sam snorts, “You still send Dad money?” 

Dean shrugs. Famously, John Winchester did not get along with his youngest. Dean knew that Sam saw their father as a drunk- one who sponged off the goodness of his eldest son’s heart. Sam had often stated that Dean was a sucker because he kept giving money to their father, but Dean thought otherwise. His father had been through a lot- a war, the loss of the love of his life- and Dean felt his father didn’t deserve half of Sam’s criticisms. 

“I might have to downgrade apartments,” Dean sighs, tossing one of the bills aside and reaches for his beer bottle. “I can’t live this part of town anymore. Shit, this was a bad time for Baby to break down.” 

Baby, of course, was Dean’s pride and joy- a 1967 Chevy Impala. 

“You still haven’t fixed her?” 

“I haven’t had the time. I spend my weekends with Emma and I’ve been trying to get this publicity launch for that shit book series that Bobby is trying to sell over and done with. Hey, do you want tickets for it?” 

“Spend a night with you, Bobby, and that neurotic writer? Yeah, I think I’ll pass.”

“Man, I hate those things. Do you think I could call in sick?” 

“You could try. Better you than me,” Sam snorts. “I wouldn’t have Bobby mad at me for anything in the world. I’m just glad it’s your ass that’s on the line.”

“Thanks for the support, bitch.” 

“Jerk,” Sam shoots back. 

-

“The _Supernatural_ series had left fans with the two brothers torn apart and about to go through hell- literally for one of them. Thanks to popular demand, I am glad to say that the series will be returning. The next collection will bring our two heroes back together and will introduce new advisory for them to fight. To talk more about this, we have the author of the series with us, Carver Edlund.” 

Dean watches Chuck slowly walk to the stage to take the mike from MC. Despite the fact the books were barely profitable, the turn out this evening had been huge, which had shocked both Dean and Chuck (although Dean thought it probably had more to do with the free beer rather than the love of pulp fiction). Just before the little announcement, Dean had seen Chuck chugging down a numerous amount of Purple Nurples that they were serving and he had to turn away from the mumbling and stuttering that Chuck considered a proper speech. Dean still has to stick around and answer questions, and he was now looking for a waiter who was serving cocktail weenies so he had something to make him look busy for Bobby. 

“How do you feel about angels?” he hears Chuck tell the crowd, “yeah, because let me tell you, they’re not as lame as you think.” 

Dean could kill Chuck. Chuck had begged (on bended knee and everything) for Dean not to reveal the introduction of the angels, and now a drunk-off-of-Purple-Nurples Chuck has the just blabbed something that Dean has painfully tried to conceal. From behind him, he can hear Bobby mutter, “idjit.” 

Chuck catches Dean’s eyes as he continues to stumble through his speech. Dean mimics the cutting of the throat and he can see Chuck wince even from where he is standing. Chuck mumbles out the rest of the speech and excuses himself hastily. 

Now that’s over, Dean wanders lazily around, munching on hors d’oeuvres until he runs into another one of Bobby’s client, Victor Henriksen, who writes True Crime novels. Henriksen is talking to a tall blonde man, whose wearing a blazer and a low V-neck sweater that screamed douche-bag to Dean. 

“Winchester!” Henriksen greets, “this is Balthazar.” Henriksen moves aside for Dean to shake hands with this Balthazar dude. There is something creepy about the man, probably with the way he eyes up Dean like he’s a collectable item and at the same time looks at Dean like he’s just a monkey in a suit.

“Dean, it’s nice to meet you,” the man says with a surprising British accent. 

“Surprised you aren’t with Sam,” Henriksen smirks. “Thought you two were joined at the hip.” 

“Whose Sam? Your boyfriend,” Balthazar says with a laugh. 

“God, no! We’re brothers. Brothers.” Dean used to travel cross-country during college with his brother and it was surprising how often people thought they were together. Like really surprising. 

“Here’s your drink. Sorry, it took so long, Balthazar, the line was long,” a gruff voice says behind Dean. Dean turns to see Castiel Novak, looking very naked without his trench coat, but still wearing a suit that looked a size too big for him. 

“Dean?” Castiel gasps, his blue eyes widening. “I’m surprised to see you here.” 

“You know each other?” Henriksen asks, chuckling lowly.

“I’m a friend of his brother, Sam Winchester,” Castiel explains. 

“Sam Winchester,” Balthazar says with the disbelief. “The big, tall one?” 

“Yes,” Castiel mumbles, looking down at his feet. Balthazar looks smugly down at the blushing man. 

“Dude, I didn’t think this lowly popular culture gig would be your thing,” Dean teases. “I’m surprised you would lower yourself to spend an evening on Chuck’s books.” 

“The _Supernatural_ series aren’t to my taste, but I was Chuck’s roommate in college and I’m here to support him,” Castiel frowns. “I thought it was your job to promote Chuck’s books, not discourage sales.” 

Beside him, Balthazar lets out a low whistle. Dean shoots Castiel look that hopefully says, “I’m going to kill you and hide your body so that you’re never found” and Castiel returns the glare with a “I don’t understand you” stare. 

“Before Cassie here left, we were talking about blow jobs,” Balthazar announces, breaking the staring contest between Dean and Cas. 

“Please Balthazar,” Castiel protests, his face turning red again. “I’m from Illinois, we don’t talk about these things.” 

“You said that the last time we met,” Dean laughs. “I still don’t understand what you meant by that.” 

“Castiel,” Balthazar laughs. “You haven’t told Dean here about your humble origins as a preacher’s son from Illinois.” Balthazar turns to Dean. “We have to be delicate around him. He’s practically a virgin. Well, almost.” Balthazar reaches over to pinch Castiel’s red cheeks, which Castiel quickly shakes off. “Ah, now he’s shy.” 

Castiel blushes again, looking back down at the floor. “Excuse me,” he mumbles, moving quickly away from the group. 

“Awww, you hurt his feelings,” Henriksen teases.

If Balthazar replies, Dean didn’t hear him. He instead follows Castiel out. 

 

Castiel is standing awkwardly just outside the front entrance, cell phone at his ear and that ugly trench coat in his arms. As Dean walks out, he hears a sigh of defeat as Castiel closes his phone. 

“Need a ride?” he asks. Castiel looks up quickly, his blue eyes widening with surprise. No man in his thirties should look so innocent. Dean swallows hard and waves his car keys at Castiel. 

“My brother was suppose to pick me up, but he was the tendency to be… unreliable at times.” 

“Hey, don’t sweat it. I’m leaving and I’ll give you a ride. My car’s just back there,” Dean says, pointing with his keys to the far side of the parking lot. 

“I couldn’t. It would take you away from the party.” 

Dean shrugs his shoulders. “I was planning on leaving anyways.” 

 

Castiel pauses when they reach Baby. 

“I should have known you drive a gas guzzler,” Castiel says quietly, moving to the passenger side. 

“I bet you drive a Yaris,” Dean chuckles as he ducks into the Impala (thankfully he’s had time to fix her). 

“I don’t drive,” Castiel states. Awkward silence fills the car. Dean pushes away the urge to turn on the radio and blast music on full volume. Instead, they drive in silence until Dean looks briefly at Castiel, who is sitting stiffly beside him. 

“So how did you meet Sam?” Dean says, breaking the silence. 

Castiel shoots Dean a confused look. “I suppose you could say that my ex introduced us.”

“Your ex?”

“Boyfriend,” Castiel replies slightly forced. 

“Man, how did that happen?” 

“My break-up or how I met Sam?” 

Dean sighs, it’s like talking with a child. “Sam and you.” 

“I used to work at Crowley and Milton, until I ended my relationship with Crowley, which made it rather unprofessional to work there. I had to switch firms.”

“Crowley? As in the other half of Milton and Crowley? You worked for your ex?” 

Castiel’s back stiffens even more, if that’s possible. “Yes, although at the time, I worked for my half-brother. He’s the Milton of Milton and Crowley.” 

Dean lets out a laugh. “I guess that brings out a whole new definition of family business,” he mutters.

“You could say that,” Castiel returns without humour in his voice. 

“So why did you guys break up?” Dean spurts out before he can stop himself. He mentally kicks himself. 

“What do you mean by that? What kind of question is that?” Castiel asks flatly. 

“I’m sorry-”

“I hardly even know you.” 

“You don’t have to tell me. I was just making conversation,” Dean snaps. Another awkward silence fills the car. Dean shifts uncomfortably as he pulls to the curb. 

“We fought a lot,” Castiel states, his voice restrained and even. It makes Dean jump in his seat as he turns off the engine. “He was… _is_ … a very brilliant man. I was tired of being overshadowed by him intellectually. Why did you get a divorce?” 

“What?” he sputters, his jaw dropping. He clears his throat, “I’ve never been married.”

“Oh, I’m sorry. Sam gave the impression that you have an ex that you still have to see.” 

“Ah, yeah, Lydia. I have a daughter with her, that’s all.” 

“Well, how did you break up? I mean, it must have been a serious relationship if you felt like reproducing with her.” 

Dean does not want to talk about this with Castiel, who according to Dean’s book is still a complete stranger. Hell, he barely wants to talk about this with Sam. 

“Emma was what we call a surprise,” he explains quickly and sharply- his way of saying ‘drop it’. “We didn’t mean to ‘reproduce’ as you put it. Anyways, Lydia left me for another woman.” 

“That must have been very demoralizing for you,” Castiel states sincerely. 

“Thanks, Cas,” Dean laughs. 

“No, that must have been very sexually humiliating for you. That explains the little girl. A 16 year-old holds no threat to your masculinity.” 

Dean’s not sure what the hell Castiel is talking about, but he thinks he might be referring to his friendship with Jo. Sam mentioned that it’s kind of creepy that a 30-year old hangs out with a 20-year-old, and Dean guesses Cas thinks so too. 

“She’s twenty, and you know what Cas, you have a losing personality sometimes.” 

“I have been told that I do no excel in social situations,” Castiel confesses blandly. It causes Dean to give the man next to him a double-take before he bursts out laughing. Cas looks at him with bewilderment. 

“Excuse me, but I need to walk my dog,” Castiel says, moving to open the passenger side of the door. 

“Sure, sure. What kind of dog do you have?” Dean says as he sobers up. 

“The worst kind,” Castiel states. Dean can see a small, private smile appear on Cas’s face. “A dachshund. According to Chuck, it’s a ‘penis substitute’ for me.” 

“Man, I would have a thought in your case it would have been a Great Dane,” Dean jokes, thankful when he hears Castiel’s low chuckle. Cas’s eyes warm with this action and for a second, Dean understands what Sam sees in him. 

“You can join me if you want,” Castiel offers.

It only takes a minute for Dean to debate between leaving and staying. He has nothing better to do and Castiel is funny in his odd sort of way. Dean hasn’t talked this honestly with anyone in a long time sans Sam. The people he spends his time with prefer discussions of sports and cars, so this is a nice change for him. Plus, he could find out more about Cas and Sam’s relationship without it looking like he’s snooping. 

“Yeah, sure,” he replies. “I know a place that has some good pie around here if you want to stop in.”

Castiel gives Dean other one of his small smiles and nods as they exit the Impala. 

 

“So Sam told me about your relationship. You guys serious?” Dean asks as they wait for their pie at the counter of the small diner. It’s nearly one in the morning and they make up half of the patrons that are present. Castiel stands next to him with his dachshund in his arms, not paying attention to Dean. “Hey, Cas,” 

Castiel looks up wide-eyed from the dog. “Huh?”

“Is it serious between the two of you?” Dean repeats. 

Castiel lets out a low chuckle, “Chuck tells me I shouldn’t get involved with these kind of situations.” 

“You went to Chuck for advice? Seriously?” Castiel shrugs. 

“Yes. Anyways, Chuck keeps telling me that I get into these situations on purpose. He says it’s what led to the situation with my ex-boyfriend.” 

Dean lets out a low whistle. “Yeah, nothing says well-balanced like sleeping with your brother’s partner.” The cashier raises an eyebrow as he passes Dean their pie. Castiel makes a motion to pay, but Dean stops him. “Don’t worry about it,” Dean insists, handing the money over to the cashier. 

“Do you want to take a walk by the river?” Castiel suddenly asks. He places his dog onto the ground. 

“Do you have idea what time it is?” Dean double-checks his watch. It’s now five after one. 

“What do you mean?” Castiel looks at him puzzled. 

“I mean, if I don’t get my four hours, I’m a basket case,” Dean chuckles, holding the door for Cas. “Hey, don’t you sleep?” 

“It just seems like the kind of night to sit outside and eat pie.” 

Dean can practically hear the angels sing with that statement. It sounds like the perfect way to spend the night and going back to his empty (even more so, since he’s moving) apartment doesn’t have much appeal. 

“Yeah, sure does.” 

 

The light of early dawn hits them gently as they sit on the park bench. Dean can’t believe he spent the entire night out and if he wasn’t so stimulated by the conversation he was having, he was certain his eyes would be drooping. There’s an empty box sitting next to them, with two plastic forks in it and smear of leftover blueberry pie on the cardboard. Castiel’s dog is sleeping at his feet, a small snore escaping every once in a while. They get up to leave when the sun fully rises. 

“Come on, Waffles,” Cas calls. The tiny dog looks up with tired eyes and slowly gets up. 

“You named your dog Waffles?” Dean scoffs. The idea of that the stiff and formal Castiel has a dog named Waffles makes him smile. Castiel blushes. 

“My brother did. He found the name… amusing. I’d better head back I have an appointment with Sam later for lunch,” Castiel says as they make their way back to Cas’s apartment. He should know better, but the mention of Sam and Cas makes that smile disappear from Dean’s face. 

“Oh, alright.” 

Dean really doesn’t want their conversation to end, but on the other hand, he is dead tired and he should head back. 

“Right, well, I’ll see you later,” he tells Cas casually. Cas nods and leaves Dean to watch the trench coat figure walk away from him. It’s then that he realizes how tired he is.


	3. Chapter 3

**Summary for the Chapter:**

> In which facts about cats are traded in deep space.

“Dean’s great, isn’t he?” Sam asks Castiel as he digs into his salad. Castiel remains silent as he chews his way through his burger. Usually they didn’t spend a great deal of time together at the office considering that Sam rarely dealt with Castiel’s department, but Sam had made a point of getting Castiel out of the office for lunch. The guy needed a little more exposure to the rest of the world, and Sam suspected that if Cas wasn’t at the office, he was spending most of his time at his apartment alone. 

“Hey, he told me that you guys ran into each other the other night at that book release party. He said you had a good time with you.” Which is not entirely true, Dean just mentioned Cas wasn’t as annoying as he originally thought he was, but in Dean speech that meant Cas is golden. 

“I thought he didn’t like me.” 

Sam sighs. The problem with his brother is that he comes off a little rough around the edges and hostile. Castiel is the sort of guy who is polished and pristine, who likes books written by Russian authors and suits over jeans and Sam can see why Dean and Cas would butt heads. Castiel doesn’t see that Dean’s smart because he doesn’t come off as such. There’s a hidden intelligence within Dean that people rarely get to see and Sam wishes that Cas could see that.

“Maybe not a first, but Dean just needs time to get use to people.” Castiel looks doubtful. “Trust me, he likes you.” 

Castiel nods and continues to eat his burger, the look of doubt slightly clearing from his face. Now is the time to test the waters with an idea that Sam has been mulling over for the last couple of weeks. 

“I think I should leave Jess,” he states slowly as he looks Castiel straight in the eye. Dean had reacted unfavourable to the idea, but Castiel was more open minded in these matters and Cas’s opinion would really help Sam make that final decision. 

“If you think that’s for the best,” Castiel mumbles, but he looks anything but happy at the idea. Castiel doesn’t even look surprised; apparently Sam’s been more than obvious about his intentions to end his marriage. 

“Yeah, but what do you think?” 

“I think the ending of a marriage is a serious matter and one that cannot be discussed frivolously during lunch. Personally, I think you should wait it out. An affair is a much shorter thing than you think.” 

-

Dean’s Sundays are spent as such: waking up at 6:00 am, making pancakes for Emma (which they then eat in front of the TV watching cartoons), helping her pack, driving her back to Lydia’s and returning to his empty apartment. This routine breaks his heart every time, but it’s not like he can change it. Lydia has custody and Dean’s life is presently not suited to take care of a child full time, which is shame because Emma’s growing up without him, and quickly at that. Plus every time Dean drops off Lydia, they fight because they’re the sort of parents who snipe at each other when they’re in the same room together and it sucks that Emma has to be raised in that environment. 

Now he’s alone on a beautiful Sunday afternoon with nothing to do. Sam and Jess have gone up to visit her parents for the weekend, Jo has a date that Dean’s suppose to cover for her to her mom, and he’s kind of stopped the whole one-night stand thing after Emma was born. Basically, he’s stuck in his apartment, which is the middle of being packed up so that he can move. The collection of cardboard boxes and empty shelves is an even lonelier sight and Dean’s itching to get out of there. 

It’s almost like he has a guardian angel, because his cell phone rings just before Dean feels like tearing his hair out. 

“Hello?”

“Dean Winchester?” a voice replies that is deep and throaty. “This is Castiel Novak. I’m a friend of your brother, Sam-”

“Yeah, yeah, I know who you are,” he chuckles. “What’s up, huggy-bear?” He can hear intake of breath on the other end. Apparently Cas hadn’t planned this far ahead in their conversation. 

“I was just wondering if you wanted to go on a walk with me?” Castiel rushes out. 

“Sorry? What was that?” Dean teases. 

“I just thought that today is extremely pleasant out and Sam’s away, so maybe you would like to go out on a walk with me?” 

Ignoring the feeling that it sounded like Cas is asking Dean to prom, he says yes, because, hell, it’s not like he has other things to do. 

As soon as they find each other at the park, it begins to rain. Not the light drizzle, pleasant sort of rain, but the here is Thor’s wrath and we’re in the middle of a hurricane sort. 

“Cas, the weather’s not really living up to what you were promising,” Dean yells, half-jokingly, although he’s pretty sure he’s been droned out by the sound of thunder. 

“It seemed like it would be a pleasant day,” Castiel apologizes, as if he’s personally responsible for the weather. Cas pulls Dean into the closest building that’s opened to the public and maybe Cas did plan it, because it’s a museum and Cas looks more delighted to be cooped up in here than outside. “Lucky for us, the museum is open today.”

Dean looks around, wiping the rainwater from his face. The museum is crowded with the people seeking shelter from the storm. Cas’s face lights up when he sees the main display- something about exploring space. Dean, whose interest in space extends only to TV (i.e. Star Trek), can’t protest with that look of delight on Cas’s face. 

“Well, lead on, Colombo,” he says, pointing Castiel to the entrance of the main exhibit. 

 

Turns out Space is pretty neat, even if Dean’s love of it extends only to stargazing and Star Trek. The exhibit consists mainly of a dark room that is lit by the light of the glowing planets in the solar system. It’s cool, but the best part for Dean is watching Cas’s face light up at each display. Cas spits out trivia at the same rate that Dean makes pop culture references, and their afternoon is traced by random tidbits that Cas spurts out and the smile that Cas makes when Dean compliments him on his knowledge. It was amazing that one person could so casually toss out so much information and Dean was beginning to suspect that Castiel Novak was a bit of a nerd. 

“I’m worried about Sam,” Castiel announces as they stand in front of Jupiter, the reds and oranges of the planet washing over their faces. Dean nods to say he’s heard Cas, but he doesn’t want talk about Sam. He doesn’t really want to hear about Cas’s and Sam’s relationship anymore. He can tell Castiel wants to talk, that he’s burning to speak.

“We had plans to hang out this weekend, but he cancelled on me. We were supposed to go see a Vivaldi concert last Wednesday and he cancelled that too. We rarely spend time together and I believe it’s because he thinks I disapprove of his personal choices.” 

Dean shrugs, “well, do you?” 

“I cannot support him with his plans on leaving his wife. You must think I’m a horrible person for not “being there” for him.” 

“No, no. Of course, not.” Dean protests. Dean thinks Cas is wonderful, except for the part where the guy only wants to hang out with him because his brother isn’t available. That part pisses him off. 

“It seems I can only have relationships with men who are prone to cheating. My ex-boyfriend’s numerous affairs were one of the main reasons I left hm. I should have ended that relationship long ago, but I didn’t want our friends to think I was deficient in some way.”

“He sounds like a dick to me.”

“He was a total ass-butt,” Cas agrees, a small smile slipping onto his face. “Too bad he’s a genius. Plus, he opened me up sexually.” 

Dean chokes on the imagery. “Thanks for the over-share, Cas.” 

Cas steps ahead of him, moving towards Saturn. “Saturn is the sixth planet from the sun. How many of the moons of Saturn can you name? There’s Titan, Mimas, Dione, Hiperion-”

“I can’t name any of them,” Dean interrupts, “probably because they never come up in conversation.” 

“Facts,” Castiel sighs, “I have a million of them at my finger tips. Did you know that a cat’s penis is sharply barbed?” 

“Um…”

“You probably think I’m too cerebral,” Castiel confesses, moving to the next planet. 

Dean stops and eyes the shorter man as he walks towards Uranus. Castiel waits patiently for Dean, turning to stare at Dean with an even more intense look. Dean shifts uncomfortably at this, because right now he just realized that he wants to kiss Cas and maybe take him behind Uranus and make love to him. He resists this primitive urge, because banging your brother’s lover is like five kinds of messed up. Instead, he shrugs his shoulders and moves to join Cas. 

“Hey, I don’t know,” he raises his hands to protest. “You are kind of on the brainy side. God knows what an intellect like you must think of me,” he says, half-joking, half looking to see what Cas says. 

“I think you’re fine. You do have the tendency to be a little hostile.” 

“Oh, thanks for that.” 

 

“So, you think I have no feelings?” Castiel says as they exit the museum. 

“Hey, I never said that,” Dean protests. “Jesus, I didn’t think you were so sensitive.”

Castiel shrugs his shoulders. “Do you want to grab dinner?” 

Dean wants to say yes. There’s actually nothing better than the thought of hanging out with Castiel, but that moment in the museum plays in his mind. As tempting as that offer is, Dean doesn’t think he can control himself if he spends any more time with Cas. If Castiel had been anyone other than his brother’s lover, he would have said yes. Sadly, Castiel is the apparent love of Sam’s life and Dean needs to leave him alone. 

“I don’t think that would be a good idea,” he states, rubbing the back of his neck. For a second, Castiel looks disappointed and Dean wants to take back his denial. 

“How about next week?” Castiel offers. 

“I don’t know.” Dean doesn’t want to be his brother’s replacement and he really doesn’t want to be the re-bound if Castiel and Sam break up. It’s better to keep at a distance. “I’m kind of busy.” 

“Oh… okay,” Castiel says, looking down at his feet. This action pushes Dean in the guts, and he feels guilty, like he should apologize. Instead, he just mutters that he has to go and leaves. 

-

Castiel is no longer sure where he stands with Sam. 

Castiel had left his previous firm after a humiliating break-up with Crowley and Sam had made him feel welcomed at his new work. It was Sam who had invited him to join him for lunch and it was Sam who made sure that Castiel got out and about so he that he wouldn’t spend his time hiding away in his apartment. Castiel is entirely grateful for that. Sam is a good friend too. He listens and he does the talking when Castiel doesn’t want to. Sam also values his opinion, something that doesn’t happen often to Castiel. Sam comes to Castiel with personal problems so often that it has allowed Castiel to share what is on his mind, something he rarely does. 

Lately, Sam has been distant. Their after-work meet-ups have been cancelled for the most part and they rarely spend lunch together. Sam had come to him a month ago, asking his opinion about Sam’s love life and Castiel had made it known (in so many words) that he had disapproved of it and Castiel suspects that this is mainly Sam’s reason for avoiding him. Although Sam is a good man, he does have faults and one of them is his extramarital affairs, which are apparently well known within the office. Before Castiel had moved offices, it was rumoured that Sam had been arrested for drunk driving with a woman named Ruby and previous he had had a passionate affair with an assistant named Madison. The office didn’t care as long as it didn’t interfere with Sam’s work, but Castiel had felt that Sam’s current lover was interfering more with his peace of mind more than the previous ones had. He had met Amelia Richardson and, despite the fact that she was smart and pretty, Castiel couldn’t see why Sam would chose her over his wife, especially since Amelia was a nervous secretive woman who was constantly keeping Sam on edge and at a distance. 

Sam had confessed to him that he wanted to leave Jess for Amelia, and Castiel had urged him (gently, as that was Castiel’s way) to rethink this action, but Sam didn’t want advice, he just wanted someone to support him. Apparently, Castiel wasn’t the only one who disapproved, as he remembered Sam complaining about how his brother was in no position to judge Sam’s personal life and that he was upset that Dean wasn’t there for him.

Dean’s another problem of Castiel’s. Once again, here is another person that Castiel isn’t sure about when it comes to in terms of their relationship. They aren’t friends, nor are they strangers, but they seem friendlier than just mere acquaintances. Although Castiel is grateful for Sam’s friendship, he has found that his best memories since his move come from Dean. Dean is passionate, but this passion is emotionally based rather than intellectually and this is so different from the lawyers he spends most his days with. Dean is humorous, or at least Castiel thinks Dean is, since Dean keeps making references that Castiel doesn’t quite understand. Dean also doesn’t seem to mind that Castiel is awkward and, in fact, Dean makes himself feel more comfortable with himself than anyone else. And it’s difficult for Castiel that Sam is keeping at a distance, because he would like Sam’s permission and advice for pursuing a relationship with Dean. 

Instead, Castiel is sitting patiently, waiting for Sam to stop complaining so that he can speak. 

“Anyways, Jess has been so needy lately. She’s never been like that, but suddenly its like ‘when are we going to have kids, Sam’ and ‘why don’t you spend more time here’. And on top of that, Amelia wants me to meet her father who was apparently in the army. Plus, Dean’s broke and won’t take any help from me, despite the fact he has to pay child support and he still sends money to our father. But Dean’s always been like that, he would rather chose martyrdom than get actual help.”

“Maybe you should end your relationship with Amelia if it is causing you so much pain,” Castiel points out. 

“Cas, I’ve explained this. Amelia and I are at this delicate point of our relationship. Jess and I are old news. I mean we had a good try at it, but it’s over. We want different things in life.” 

Castiel snorts. He’s heard this before. It’s a classic excuse, and that’s all it is. He’s not supporting Sam on this one. 

“Sam, I have refrained from commenting about how I really feel about you and Amelia because I do not want your feelings hurt, but if you insist on continuing this affair without considering the consequences of your actions upon the people in your life, I’m afraid I have to end our friendship as I can longer support you. Amelia is a nice woman, but Jess is everything good that you need in your life. She was your motivation for law school and she helped support you. You need to realize that you cannot continue to cheat on her and expect that she will never find out.”

Sam sits there for a moment with a stony look upon his face. “Wow, Cas. I thought at least you would support me in this since no one else has.” 

“I have explained to you the reasons why I cannot,” Castiel states calmly. “It is for my own personal feelings that I cannot, and is nothing against you as a person. If you had taken my advice, or maybe your brother’s, who I assure you is acting in your best interest, you would be happier.” 

“I should have known better than to come to you for advice considering the fact that you left your previous office because your ex was banging your best friend’s wife and everyone knew long before you did,” Sam snaps. 

Castiel knows that Sam is acting out in anger, but that doesn’t stop him from getting up and leaving. He’ll forgive Sam for that one day, but today is a different story. 

-

Dean is surprised to see Castiel at the door of his new apartment. Castiel’s eyes are red and he sniffles a little as Dean lets him in.

“I’ve just had a fight with Sam,” he states as Dean shuts the door. “Could I have a glass of water?” 

There’s a rush of anger for Dean. He doesn’t want be the _friend_ that people go to when they fight with their lovers, especially when it comes to Castiel. This sort of relationship is going to hurt him, but that doesn’t seem to stop him for letting Cas in. 

He walks over to the sink and grabs Castiel a glass of water. “The waters a little brown,” he tells Cas as he hands the glass to him. 

“I shouldn’t be bothering you,” he states. “Oh wow, that’s really brown,” he says with a watery chuckle. 

“Thank you! Jo said I was overreacting when I showed her.” 

Dean’s new apartment is a step down from his previous, but he can afford it easily and he doesn’t have to live on Ramen Noodles for a month like he’s a college student. The place is fine, even if the neighbours are little bit wacky. He swears his upstairs neighbour’s favourite hobbies include strangling small pets by the sound of it and the elderly neighbour across from him keeps trying to grab Sam’s ass when he visits (which is a sure sign that she’s senile because looks who she’s living across from). The first night he could barely sleep and he’s beginning to depend on whiskey-induced slumber. 

“I guess I deserved it,” Castiel mourns as Dean searches the apartment for tissues. “I know I shouldn’t pry into people’s private lives.” 

“Hey, don’t do that. It’s Sam who’s the problem, not you. Hell, I’ve tried talking to him and he won’t listen. And I’m his big brother! He’s supposed to listen to me! Anyways, these sorts of relationship are always bad. It confirms your worst feelings that you don’t deserve happiness,” Dean yells to Cas as he searches his bathroom. 

He re-enters the kitchen with a roll of toilet paper for Cas to use. Castiel doesn’t seem to mind this and he grabs it and starts blowing his nose with it.

“I really don’t need you to psychoanalyze me, Dean. I have Chuck for that.” 

“Chuck? I mean, really? Is he the best you’ve got? You shouldn’t be taken the advice of anyone who calls you up at 4 am to weep in the telephone.”

“Chuck does have an… unorthodox approach to writing. But I find he’s been really helpful.”

“I can tell. I wish I had your self-esteem.” 

Castiel lets out a small chuckle. “What’s that?” he scowls as he blows his nose. Dean’s upstairs neighbour was just beginning his daily ritual of pet sacrifice- or at least that what it sounds like to Dean. 

“Can you believe I live with that?” Dean asks with a laugh. “I swear he’s strangling a parrot up there.” 

“That’s appalling,” Castiel agrees, but there is a small smile on his face. “I better go.” 

“Hey, I’m meeting up with Jo later at the Roadhouse for drinks. Do you want to join us?” It’s Dean’s cure-all for messy break-ups- the drink until you can’t feel method. 

“No, I’ll be fine.” Castiel blows his nose loudly, almost drowning out the noise coming from upstairs.

“That’s a healthy piece of toilet paper you got there,” Dean tells Cas with a snicker. Castiel gives the toilet paper roll a puzzled look before he lets out weak chortle. 

“Thank you, Dean,” the shorter man tells him sincerely. “You’ve helped in more ways than you can imagine.” Just as he leaves, he turns and gives Dean a peck on the cheek. The action is weird and out of place- very much a Castiel move- and leaves Dean standing there stunned.

**Notes for the Chapter:**

> Sorry this took so long to update. I've been busy with exams for the last week, but they will soon be over and I'll be free to truly procrastinate over updating.


	4. Chapter 4

**Summary for the Chapter:**

> In which Dean acts like a little girl in love and deservedly gets teased for it.

It’s been two weeks since Castiel kissed Dean, and Dean’s still in shock, which is pretty pathetic on his part. Cas only kissed him on the cheek and here he is still mooning over it like Olivia Newton John’s character from Grease (and the only way he knows he’s acting like this is because Jo keeps humming “Hopeless Devoted” every time he walks into the same room as her). He’s mentioned a little bit of the situation to Jo and all she said was for him to stop sulking. 

He’s not sulking.

He’s just stopped hanging out at the Roadhouse after work, and spends most of his time in his apartment watching TV (and telling people he’s unpacking) and ignoring his brother’s phone calls. He no longer goes out for lunch, instead he chooses to eat at his desk, or at least he did until Bobby got tired of seeing him there and forced him to eat lunch with him. 

“Don’t you have any friends?” Bobby mumbles as Dean joins him for lunch once again. It’s a dismal picture- the two of them crowded in Bobby’s office, but Bobby doesn’t like anybody and Dean has nowhere else he’s willing to be. 

“Shut up and eat your salad,” Dean retorts as he unwraps his sandwich. “Since when did you start caring about your heart?” 

“Since my doctor told my wife about my test results. What the hell are you eating?”

“I call it the Turducken. It’s the mixture of the best birds in town- turkey, duck and chicken.” Yeah, it’s amazing how inventive Dean gets when he hasn’t been grocery shopping for two weeks and he barely has enough food in his kitchen for a sandwich. 

Bobby looks absolutely disgusted. “That just ain’t right.” 

“Yeah, well, so is eating grass, but that’s not stopping you,” Dean snaps back. 

“Jesus boy, did you and Sam’s cycles finally sync? You both been acting like the world’s personally out to get you.” 

“You’ve talked to Sammy?”

“He’s worried about you. It seems like you haven’t been returning his calls. Not that I blame you. Talking with him like defusing a time bomb with a butter knife. What’s got his goat?” 

“Oh you know, his inability to keep it in his pants is making his life miserable. Apparently he’s outgrown Jess and he’s thinking about divorcing her.” 

“I guess that would make a man grouchy. What’s so special about this girl to make him think about leaving Jess?”

“Probably the fact that _she_ has a penis. Turns out Sammy’s in love with his co-worker, this guy named Castiel. I’ve met him. He’s nice, but I don’t see why Sam would leave Jess for him.” 

“You think he’ll go through with it?” Bobby says, unbothered by the fact that Dean just announced that Sam apparently likes dicks now. 

“Nah, Sam’s just in the high of his relationship. Once it cools, he’ll be back with Jess and everything will be fine again.” 

“And would this new guy in Sam’s life be the reason you’re acting all like Aunt Flo’s been visiting?” 

“He’s part of the reason,” Dean admits. “Like I’ve said, he’s nice, but it’s not worth it for Sam to leave Jess for him.” 

Also there’s the fact that Dean sort of likes the guy and doesn’t think his brother (as much as he loves his brother) deserves him. No matter what Dean is feeling right now, he shouldn’t get between Sam and Cas.

“Yeah, well, it’s best to let your brother live his own life and you live yours,” Bobby mumbles as he picks at his salad. 

-

**Just wanted to thank you for helping me out the other day. Have cleared things up with Sam.  
-Cas**

**As a thank you, would you mind if I buy you a pie?  
-Cas**

**It doesn’t have to be strictly pie. I do know other places that sell other confectionaries if you are interested.  
-Cas**

**I suppose you’re not. Maybe dinner then?  
-Cas**

 

Bobby’s advice is great, except for the part where Sam’s personal life keeps texting Dean. Dean thought if he ignored them long enough, Castiel would stop texting, but apparently the part where he doesn’t excel in social situations applies to non-verbal communication. 

Dean doesn’t mean to be rude, but he’s not sure how he’s suppose to tell Castiel that the reason they can’t hang out is because he gets a hard-on when he’s in the same room as Cas. It’s not just a boner, but a boner mixed with jealously because he knows that he _can’t_ have a chance with Castiel, and Dean doesn’t know how to convey that through a text message. 

Instead, he deletes Cas’s messages. 

-

“It was then that I realized that I had entered a relationship with a classic butch-male stereotype- one that was always overcompensating in fear that any action he performed would be perceived as that of girly or unmanly, a trait certainly introduced by his militaristic upbringing. This was a man who firmly believed that masculinity was based on womanizing, heavy drinking, loud music and classic cars- all tropes befitting of a midcentury patriarch,” Sam reads out loud. Bobby nearly choked on his beer and Dean was sitting next to the two, his face bright scarlet. 

“Yeah, well, that’s enough,” he mumbles, taking a swig of his beer. 

“No, no, this is great!” Sam insists. “Tell him Bobby, this is great!” 

“I have to say, I’m beginning to see another side of you Dean,” Bobby chuckles. 

As Friday nights go, this one sucks. Dean’s personal life has gone down the drain, but he didn’t think it sucked to the extent that he would spending his Friday with his little brother and his boss. He also didn’t expect Sam bring along his copy of his ex’s book- _The Amazonian Woman- How I Left the Patriarchy To Find Myself_ , which was a “fictional” tell-all about their former relationship. Dean had tried to sue, but Sam said that since it was clearly stated that it was as a piece of fictional work, there was nothing they could do. Still, that didn’t mean Dean wanted his personal life read out at his favourite bar. 

“Listen to this, Bobby,” Sam states gleefully, “Soon, I discovered that this classic butch figure was nothing but a façade- one created to hide a little boy with daddy issues and a fear of showing off true emotions. Every thought said out loud had to be a punch line to hide the insecurity and low self-esteem this man had. Despite his attempts at uber-masculinity, it was painfully obvious that he was overcompensating for his homosexual urges, which he had been forced to deny since adolescences. He was never good at hiding his inner homosexuality, as it was evident just from observing his face when he watched his favourite show _Doctor Sexy_ , in which it was obvious that he was madly in love with the male lead-”

“Okay, that’s enough,” Dean yells, as he snatches the book away from Sam. Not that Sam notices, as he’s yowling with laughter at this point. Bobby can’t even hide the grin on his face and he’s leaning into Sam as they laugh. Honestly, if Dean had a chance, he would burn every copy of this book, along with that stupid _Supernatural_ series. At least the series was making him money. “This book is total bullshit.” 

“I don’t know Dean, I remember those _longing_ gazes you gave Doctor Sexy whenever you watched that show,” Sam says between laughs. 

“Jesus, when did you get into such a good mood,” Dean snaps. “The last week or so you’ve been a total bitch to talk to.”

That sobers Sam up quickly. “What do you mean by that?” 

“I just mean that since you and Cas fought, you’ve been kind of snappy. Bobby agrees with me.” 

“Hey! Don’t bring me into this,” Bobby mumbles, taking another swig of his beer. “I’ve got nothing to do with you two idjits.” 

“Well, Dean, since you haven’t asked, I’ve sort of cleaned up my life a little bit. I’ve apologized to Cas for my behaviour before.”

“Good, he deserves better than your crappy attitude.” Dean ignores the confused look that Sam sends him. At that moment, Dean’s phone begins to buzz. He quickly looks down at it. 

_**Castiel Novak**_

He quickly presses the ignore button and looks up to Sam and Bobby, who are both eying him suspiciously. 

“Are you alright Dean?” Sam asks him in his caring brother voice. 

“I’m fine,” he snaps back. “I just don’t like being humiliated in public, that’s all.” With that, he picks up the copy of Lydia’s book and storms out of the bar, missing the concerned look passed between Sam and Bobby. 

-

“Have I done anything to offend your brother?” 

Sam’s thankful that his lunch schedule has gone back to normal. He knows he’s been ignoring Cas lately, but what with this thing with Amelia and the fact that Jess is becoming more and more suspicious, well it was best for him to call it off with Amelia and focus on his relationship with Jess. The ending of their affair had been bitter, but on the bright side, Sam no longer felt like he was ignoring his best friend. 

“Um… not that I know of. Why?” 

“It appears that I have. He’s been ignoring me.” 

Odd, as it seemed that Dean liked Cas- to the point of being defensive about him. Sam hadn’t heard much about what was going on between the two of them, but lately when he talked to Cas, it had been mostly been about how he been spending some extra time with Dean. Cas was many things, but discreet wasn’t one of them, and Sam was like 90% sure that Cas had little crush on Dean. This was great news for both Dean and Cas as both were in dire need of getting laid (facts were facts). Sam wasn’t sure how Dean felt about Cas, but he was certain that Dean liked Cas enough to hang out, as Dean didn’t suffer fools gladly.

“Are you sure he’s ignoring you? Dean sometimes comes off as hostile.” 

“Well considering he hasn’t answered any of the texts or calls I’ve sent him, I believe it’s safe to say that he’s ignoring me.” 

“Huh,” Sam states, which is all he’s got since that’s classic Dean behaviour- anytime he might be getting close to someone and he decides to destroy that relationship without considering the other party’s emotions. Sam’s not really sure what to say to Castiel. 

“I’m sorry my brother’s a dick sometimes. I could try to talk to him,” Sam offers. Dean’s going to get it (along with Sam’s number one bitchface and his best lawyer/ brother rant) because Castiel doesn’t deserve to be treated this way. “But seriously, he can be pretty stubborn at times and if he doesn’t want to talk to you, he’s not going to talk to you. I would let up.” 

“I appreciate the advice,” Castiel mumbles. Sam hopes Castiel isn’t too hurt by his brother’s rudeness.


	5. Chapter 5

**Summary for the Chapter:**

> In which Dean finally discovers Sam's real relationship with Castiel and gets some advice from Bobby whether he asked for it or not.

Dean loves his brother, he really does, but sometimes Sam is a pain in his ass. The thing about Sammy is that he was all about talking about emotions and feelings. It was important to him to share and talk- although Dean’s not sure where Sam learned this from because both himself and his father were not known for their emotional openness. Fortunately for Dean, Sam’s been too wrapped up in his own problems to worry about Dean and Dean’s emotional well-being. The last couple of months have been peaceful in that respect. So it had taken him by surprise when Sam called him up and asked if they wanted to meet up for drinks. If anything, that should have been the first clue. 

“So, have you talked to Castiel lately?” Sam asks like he hasn’t been planning on bringing up this topic all night. Once again, they have found themselves at their usual booth at the Roadhouse with two beers between them and an endless supply of bar food. 

“No. He’s your boyfriend, why would I be talking to him?” Dean scoffs, taking a sip of his beer. 

Sam shrugs and Dean can see him shaking his head in the corner of his eye. “You guys have been hanging out a lot lately. Thought you two were friends.”

“Nah, he only hangs out with me when you’re busy. I’m your replacement.”

“You really think that Dean? I think you’ll find that there is a vast difference between our personalities. You’re a piss-poor replacement for me,” Sam laughs.

“Hey!”

“I’m just saying, he’s _not_ hanging out with you because he has no one better to spend time with.” 

“I don’t know if I want to thank you for that comment or smack you.” 

Sam doesn’t say anything, just digs into the peanuts in front of him. They rest in socially acceptable silence until Sam decides to open his big mouth again.

“But seriously, why have you been ignoring Cas?” he says, his eyes widening to the unbearable ‘puppy-eye’ thing that he does. 

“I haven’t been ignoring Cas. I’ve been busy.”

“With what?” Sam cries out. “You’ve been sitting at home watching that stupid doctor show and Mexican telanovelas for the last three weeks. The only people you see are me and Bobby and the only reason you see Bobby is because he’s your boss!”

“Bobby didn’t tell you that I spend lunch in his office, does he?” 

“And you spend lunch hours in his office! _Dean_!” Sam whines. “Just call him or answer his texts.” 

“I can’t, Sam!” Dean snaps back. 

“Why not? Did he do anything to offend you?”

“Because you two are dating and I have feelings for him! I mean not dating, but having this serious and passionate love affair. And he kissed me! Not on the mouth, but still, he kissed me like I meant something to him. I didn’t mean to get between the two of you, Sammy, but he did kiss me firs-”

“Sorry, what? Did you say I’m dating Castiel?” 

“Um… yeah… you guys are dating.” 

Sam’s shoulders begin shaking. Sam doubles over and collapses onto the table, his entire body vibrating with laughter. He’s laughing so hard that a couple of people in the bar turn to stare at them. Dean moves further into the booth. Even Ellen, whose cleaning some glasses shoots them a concerned look. 

“You think me and Castiel are dating?” he chokes out. Dean can see tears starting to run down his brother’s face. “ _Really_?” 

“So let me make this clear,” Dean raising his voice, “you and Cas aren’t an item?” 

“God no! Dean you know I’m straight. What could have possibly led you to think that Cas and I are together?” 

“I don’t know, how about the fact that when you introduced us, you said that he was your lover that we were talking about the other night.” 

“No I didn’t! Were you even paying attention to me? I was telling you, Jess and Jo about how I had a new co-worker.” 

“You said your lover was high-strung and nervous,” Dean points out. 

“ _She_ is. But she’s a girl, Dean! I met her when I took Riot to the vet. She’s a veterinarian- Amelia Richardson.” 

“Um…” he says, as right now that’s the only thing he can say. His mind is running through every mention of Cas that Sam has made. Dean’s feeling pretty dumb right now, and he’s had some dumb moments in his life (like dropping out of high school and only getting hired at a decent desk job because Bobby took pity on him and hired him). “So you weren’t having an Elton John moment?” 

“I told you, I’m straight and I was having an affair with a _woman_. Cas is free for the taking for all I know. Is that really why you’ve been ignoring Cas?” 

“Yeah! I thought he was your man. Didn’t want to intrude on your Moose territory,” Dean jokes. Sam shoots him another bitchface before looking all serious again and leans in with a hand out like he wants to touch Dean’s hand. 

“You owe him an apology,” Sam states sincerely. 

“I know.” Fuck, does Dean know that.

“You were acting like a dick to him,” Sam continues. “Like if I were him, I wouldn’t forgive you.” 

“Good to know you have my back, Sammy. Wait… you said, ‘I was having an affair’. Did you guys break it off?” 

“Yeah, it turns the reason she’s been all secretive and super- nervous is because she has a husband. Best to leave before someone got hurt.” 

“Like Jessica?” 

That smacks the smile off of Sam like nothing else. It’s hard not to feel bad for the guy Still, Dean has sat back and let Sam and his affairs dance alone, now it’s time for him to step in and give his brother some good-old older brother advice. 

“You know I’m not the only dick here. Jess doesn’t deserve to be treated this way. I mean, you’re married Sam! You said the vows and you should stick with them. If not, get a divorce and stop dragging her through your shit. Tell her.”

Sam looks at him like a chastised child. “You think I should tell Jess about the affairs?”

“I think you should stop lying to her. Like I said, she deserves better than that.” 

Sam doesn’t say anything, which tells Dean more than enough. They pay for their beers and leave without talking, and Dean hopes he hasn’t screwed up Sam’s marriage too much.

-

For the first time in weeks, Dean is somewhere other than his apartment, work or Ellen’s bar. Tonight, Dean finds himself at another party to celebrate that stupid _Supernatural_ series. It might have been a positive change from his usual moping around, but still, that doesn’t mean he’s happy about it. Instead, he’s drinking in the corner of the room, trying to avoid talking to other literary elites and the grabby hands of middle-aged drunk women. 

Bobby’s having a blast just to spite Dean. Dean can see him in the centre of the room with a group of people, all of them laughing at some dumb joke Bobby has said. Suddenly, the crowd begins to disperse and to Dean’s horror, he could see Bobby walking towards him with a shorter stout man next to him. 

“This is my assistant, Dean,” Bobby introduces. The man next to him shakes hands and looks over Dean like a butcher might look over cattle. The man doesn’t look imposing; he’s short, round, balding, and dressed entirely in black with the exception of a red tie. Still, there’s something about him that makes Dean wary of him. 

“This Crowley, he’s the other half of Milton and-”

“Milton and Crowley,” Dean ends. “Yeah, I’ve heard of you.” 

Right before him was Castiel’s ex- the guy who apparently taught Castiel everything he knows and had “opened Castiel up sexually”. Castiel must have been a virgin when he met Crowley because this dude looks like the sort of guy whose severely lacking in the bedroom department. If he weren’t in front of Bobby, Dean would have laughed out loud. Instead, he hides his smirk as he takes a sip of his wine. 

“Only bad things I hope,” Crowley quips, his British accent throwing Dean off a little.

“Not from what I’ve heard,” Dean mumbles, thankful when both Bobby and Crowley miss that. 

“I’ve been talking with Crowley about what would happen if we sold the rights of _Supernatural_ so that it can be made into a movie.” 

“Someone wants to make that series into a movie?” Dean blurts out. 

“We’ve had two offers,” Bobby explains slowly as if he’s talking a child. “Movie or a TV series. Chuck wants a movie, but I want a TV series.” 

“I would highly recommend the TV series- if it works out you would have a solid paycheck for the next 10 years.” 

“There’s no way it would run that long,” Dean scoffs. Crowley eyes him oddly before he turns to Bobby. Dean stands next to them as they talk, but he misses the entire conversation as he’s lost in thought and these thoughts were mainly about Castiel and Crowley together. He wouldn’t say he was seething in jealousy at the notion of Crowley seeing Cas naked, but he was certainly getting a little hot around the collar and the room suddenly felt incredible small. Finally Crowley leaves and Bobby turns to Dean with a big grin on his face- usually a sign for Dean to be worried. 

“Well don’t you look like the cat that caught the cream,” Dean teases, his face still feeling incredible hot. Bobby snorts. 

“That man will be making us plenty of money, and don’t you forget it.”

“He’s going to be causing us tons of trouble. I can’t believe that Castiel went out with that creep. I mean, when Cas described the guy I was thinking he was six feet tall, muscular and dark haired sex god.” 

“Boy, I don’t want to hear your fantasies!” Bobby says, choking on his drink.

“Yeah, well the way Cas described him, I thought I could never live up to his expectations of sex. Crowley’s no threat! I mean, look at him!”

“I don’t know,” Bobby mumbles, “he’s not bad looking. Anyways, what’s going on between you and this Cas guy? He isn’t he your brother’s butt-buddy.” 

Dean grimaces at the image. “Yeah, well, I might have gotten the wrong end of the stick on that relationship. Apparently, Sam doesn’t like dick and he’s been banging this crazy vet for the last couple of months, not Cas.” 

“I should’ve know that you can’t be trusted to run your own romantic life,” Bobby laughs. “So you’ve fucked up again.” 

“I resent the again,” Dean mumbles. 

“But I don’t see you protesting the part where you messed up.” 

“Yeah, I’m willing to admit when I’ve made a mistake.” Bobby looks at Dean in way that Dean just needs to spill the beans. “I like Cas,” he states.

Bobby grunts, “Like I haven’t noticed.” 

“I liked Cas even when I thought he was um…”

“Doing the horizontal tango with Sammy?” Bobby suggests with a smirk on his face.

“I need to find you a hobby or something. Yeah, but see I thought him and Sammy were together and I didn’t want to say anything so I… so I ignored him. Now I find out that Sammy doesn’t even like dick and had nothing to do with Cas, and I’ve been acting like an ass this entire time.” 

“Old habits are hard to break,” mutters Bobby. 

“I don’t really know what to do,” Dean confesses, feeling more vulnerable than he should in a dinner jacket and with a glass of wine in his hands. He feels out of place- usually his discussions of feelings (if they occur at all) happen in smoky bars, partially drunk on whiskey or beer. 

“Well, have you tried picking up the phone and calling? Because if I were you, that would be where I start.” 

“Like that hasn’t occurred to me,” Dean snaps. It has- multiple times. But every time he has the phone in his hand and his thumb on the call button, he freezes. He’s been ignoring the guy for a couple of weeks now and Dean’s afraid of the icy reception he will receive when he calls. It’s not like calling a girl back in high school when you know that she’ll act all mad at first and then forgive you. Castiel is grown man and he’s not going to take kindly to being ignored. “I just can’t.” 

“Well, I don’t know what to say, Dean. I guess you’re just going to have to slip on your big girl panties and call him.”


	6. Chapter 6

If there is anything more nerve-wracking than the dial tone of a call you don’t want to make, Dean has yet to face it. He’s over thirty and right now his heart is beating so hard he can barely think. After a lot of thinking (and a little bit of whiskey) Dean decided that it was best to take Bobby’s advice. Sadly, it had taken him over half an hour to man up and call the guy without hanging up before the phone even dialled out. Finally the ringing stops and there’s a moment of painful silence before he hears the gruff voice of Cas. 

“Hello?” 

“Um… hi, Cas, this is Dean…” He waits for Cas to reply but there is nothing. “Um… Dean Winchester,” he clarifies. 

“Yes, I know who you are. What do you want?” If there was any cheer in Castiel’s voice when he answered, it’s gone now and the voice talking to him is cold.

“I wanted to talk to you,” Dean says, his voice strangled. For someone who had a reputation of being cool and smooth, he’s failing to live up that image right now.

“I’d gathered that, otherwise you wouldn’t have called me. I’m asking what you want with me? Since you’ve have stopped any attempts I’ve done to try to contact you, I assume it’s not my company.” 

“Yeah, I know I’ve acted like an ass for the last couple of weeks, but if I could talk to you like face to face, I could explain.” 

“You are quite capable of talking to me right here,” Castiel states. Dean lets out a low frustrated growl. 

“I _want_ to see you. It would be easier for me-”

“Astonishingly, Dean, I don’t really care if it’s _easier_ for you, since you were the one who did the snubbing and not me. Now if that’s all you want, I think I would like to decline. Goodbye Dean. And please, don’t try to contact me.” 

Castiel hangs up, leaving Dean to listen to the dial tone. 

It’s probably more than Dean deserves- the fact that Cas had let him keep talking long after the initial hellos, was a totally surprise to him. He’s done his piece, he had tried to apologize and Castiel has refused to listen. Nothing else could be done. He could try to get Sam to talk with Castiel, explain the situation to him, but it was douche-bag move to make and only cowards send their brothers in to fight their own battles. He could stop by Castiel’s apartment and try to reason with him there. The image of a door being slammed in his face was a painful one, and Dean was certain that would be the only thing that Cas would do if Dean just showed up unannounced. Right now Dean’s head is swimming with indecision and he can’t make up his mind. Maybe a drink and a talk at the Roadhouse would help him along. He decides to do just that before the tinny- sound of “Smoke on the Water” blares in his hand. 

“Hello, Dean Winchester speaking,” he says as he picks up. 

“Dean,” Castiel states, his voice a low growl in Dean’s ear. “You’re not allowed to sit there and think that because you called me that everything is forgiven between the two of us.”

Castiel’s voice is steadily getting louder- to the point that Dean can hear Castiel’s dog barking in the background. 

“You’re not allowed to spend a great deal of time with person and then ignore him, making him feel like a stalker every time he tries to contact you. I _gave_ you a chance, multiple, but you seemed fit to ignore them. So if it appears that I am coming across as rude, I don’t really care.” Castiel says slowly. 

“Cas, I really didn’t mean to-” Dean tries to say.

“To hurt me? No, I didn’t really think you started out with the intention to do as such.” Dean can still hear the dog barking the background. “But sadly, that has been the result of our friendship. You made me think that you really liked me, that you really enjoyed my company. It may surprise you, but that doesn’t really happen to me on a regular basis. Anyways, any nostalgia I had for you is gone.” 

For the second time that day, Castiel hangs up on Dean. If the first phone call had been discouraging, the second one had left Dean feeling guiltier than he thought humanly possible. Whatever hope he had of making things up with Cas had been wiped out before Dean could even map out the plan. It seemed like an even bigger sense of failure, but he turned to the whiskey bottle brought out for courage and began drinking from it to push away whatever feelings he held at the moment. Tomorrow he could face the day, hung-over or not, but tonight he felt like wallowing in self-pity. 

-

Or at least that’s what he told himself. If the moping of pre-Castiel phone call was painful and childish, Dean’s mental state after his talk with Cas was just downright pathetic. Bobby’s extension of caring had worn out long before Dean had made that phone call, and it certainly didn’t reappear after. Bobby just ignores the sight of Dean eating at his desk and no longer tries to correct it. Finally, after three days of this, Bobby stops in front of Dean’s desk and just barks out “if you want a pity-party, you’ve come to the wrong place. Why don’t you take a couple of vacation days and come back when you’re more the little miss sunshine who used to work here.” 

It almost feels like Bobby’s firing him, but Dean still follows his boss’s advice and takes the next week off. He plans on continuing doing what he does when he comes home from work (watching TV in his boxers, eating cheetos and falling asleep on the couch) but on a grander scale. If he needed another sign that the universe is against him, it occurs when the phone rings just as soon as he returns to his apartment. 

“Hello?” he mumbles out. 

“Dean Winchester, you better be ready to go out in ten minutes,” Jo announces on the phone. “My shift just ended and I have been told that someone here needs a little cheering up.” 

“Bobby called you?” Dean says with surprise. His relationship with Bobby sometimes crosses the line of boss and employee, but never has Bobby called one of Dean’s friends. 

“Yeah, he said something about you being a whiny bitch and that you weren’t allowed back at work until you’ve cheered up. I never thought I hear Bobby saying he wanted someone perky working at the office but there you go.” 

“He didn’t actually say all that, did he?” 

“Not the whiny bitch part in so many words. I’m just summing up what he essentially told me. Now should we do what Winchesters and the Harvelles do best- drink and hustle pool.” 

-

Even if Jo is a head shorter than Dean, weighs like a hundred pounds and looks she couldn’t lift over ten pounds, Dean is terrified of her. Which is mainly why he agreed to go out. Jo keeps to her promise of an evening filled with booze and pissing off the newcomers (much to her mother’s protest). They’ve made a killing that night (or at least Jo has, she’s ruthless when it comes to pool) and instead of saving that money like the good responsible adults that they like to pretend they are, they were spending it on the best whiskey that Ellen can provide. 

Either Jo has been dumping perfectly good whiskey or she’s more heavy weight than Dean thought, but she’s no way as tipsy as Dean feels at the moment. It’s like she planned this in advance, because just after Dean settles in at the bar for the evening, she sits next to him with a look that says “we’re talking about your emotions whether you like it or not”. 

“So you fucked it up with Castiel,” she states. 

“I resent that,” he protests, even if it’s true. She just rolls her eyes and takes a swig of her drink. 

“And this Castiel guy has decided to refute any attempts you’ve made to apologize.” 

“Yeah.”

“Well he’s a jackass.” 

“No,” Dean protests, “he’s really not.” 

“Yeah, well, it’s not like he’s making your life any easier. If he gave you a chance instead of making you feel like crap, you could both be happy, but he’s wallowing in self-righteousness about how you treated him.”

“You really can’t blame him.” 

“He sounds like a stubborn bastard. It’s best to get over those types of guys and move on.” 

It’s Dean’s turn to roll his eyes. “Yeah, I’ll just slip out of my feelings for Cas shirt, burn it, and move on.” 

“I’m not saying you need to get laid to move on. I mean you can’t stop your entire life for this guy. He’s not going to start caring about you because you’ve been moping around in your underwear, eating nachos and watching re-runs of _Doctor Sexy_.” 

“It’s actually that Spanish soap that Bobby introduced me to.” 

“Whatever. I’m saying you need to get out of the house, visit your daughter more, focus on work and clean your goddamn apartment. I had to wade through the junk-food wrappers the last time I visited you.” Jo turns to her whiskey with a visible shudder. “You should also call Sam. He’s not in a great place right now either. I can’t believe you’ve ignored his phone-calls.”

“Yeah, well, I’m more scared of you than that overgrown teddy-bear,” Dean chuckles. “And what do you mean he’s not in a great place. The last time I saw that kid, he looked like he had rainbows shooting out of his ass.” 

Jo looks at him with surprise. “Jess left him.” At that, Dean chokes on his drink. “You didn’t know?” 

“Obviously. If I had known that I would be with him, not with you hustling pool. When did this happen?”

“Um… just a couple of days ago. He told Jess about the affair- all of it. She moved out the next day.” 

“Shit,” he says, because that’s all he really can say. Not only has he fucked up with Castiel, but he also left his little brother alone in what is now he’s greatest hour of need. 

“Why I am still talking with you?” Dean jokes, although his voice is low and serious. 

“Yeah, why are you?” Jo says, giving him a small smile that says she’s giving him permission to leave. 

“You’re the best,” Dean says, pressing a kiss to Jo’s forehead. 

“I know,” she says, patting him on the arm. “I’ll get Ash to drive you over.” 

-

Sam looks surprisingly okay when Dean knocks on the door of his brother’s house. His eyes are red and he has a fair amount of stubble, but he doesn’t look like he’s been drinking and crying for two days straight. 

“Dean,” Sam says, almost as if he’s taken aback by the gesture of Dean showing up. This hurts, and makes Dean feel like an even bigger jerk than usual. 

“So I heard about Jess,” he says as an explanation. “I guess my advice kind of sucked, didn’t it?” 

Sam lets out a watery scoff, but opens the door so that Dean can come in. “No, you were right. I shouldn’t have lied to Jess. I should have _never_ cheated on her. I honestly don’t know what I was thinking,” he tells Dean as they move to Sam’s kitchen. “Actually, she reacted better than I thought. She told me she just needed space right now, time to think. I had to give her that.” 

Dean lets out a low whistle as Sam hands him a beer. “That was-”

“More than I could ask for. So I talked to Cas,” Sam says, giving Dean a pointed look. 

“I came here to talk about you, not about my love life.” 

“What else can you say, Dean? That you’re sorry? That you knew that from the moment I began seeing Madison that I would end up losing my wife? I don’t need to hear it.” 

Dean nods and sits himself down. “You know I’m not always there for the emotional stuff, but I am here if you need me.” 

“Thanks, Dean,” Sam mumbles, opening his beer. “Do you just want to hang out and watch _Star Wars_?” 

Dean nods and they move to the living room. Sam falls asleep first, leaving Dean with the image an overgrown moose that doesn’t quite fit on the couch before Dean too falls asleep. 

-

If Sam could move on with his life, than Dean should be capable of doing the same. It’s not like his wife left him. He just screwed up a friendship and a potentially great relationship. So he takes Jo’s advice and begins focusing on work, begins working out (to get rid of all that Cheetos-fat he has gained), and arranged for more visiting hours with Emma. That’s another battle entirely since Lydia wants Dean nowhere near Emma. A quick call from Sam sorts that out and Emma now gets every weekend and certain days of the week that Dean can get off ( _will get off_ because secretly Bobby’s a softie and Emma has him wrapped around her little finger). If anything, Dean is now in a better place in his life than he has been in years. 

“Emma-bear,” he scolds one Saturday afternoon. Emma is currently eating cheerio’s, and missing her mouth because her lap is covered in them. She just grins at him and continues with her attempts of eating breakfast. It’s a grin that Sam says she takes directly from her father, and he knows his little girl doesn’t just have Bobby whipped. 

“Park, Papa,” she cries out as he lifts her from her booster seat. 

“You know most kids your age would be begging to watch TV all day,” he tells her, although she’s ignoring him in favour of trying to pick up her little sneakers. “Okay, hold your horses, kid,” he says as sits on the floor, slowly prying her shoes away from her. “You still need a bath before you go out.” 

She pouts but doesn’t protest when Dean picks her up and carries her to the bathroom. One surprisingly un-messy bath later, they’re on the way to the park with a bag of bread to feed the ducks there. It’s the perfect sight for Dean, watching Emma as she chases after ducks and as she throws pieces of bread at the un-amused birds. He quickly snaps a picture of her being chased by a duck for Sam, sending it with a smirk. That smirk quickly disappears when he looks up to see that Emma is nowhere in sight. 

“Fuck,” he mutters, quickly jumping up from the park bench he is sitting at. “Fuck,” he mutters again when he sees his daughter bent over and petting a dog with a man wearing a trench coat holding the leash.

-  
As it was custom, Castiel had spent most of his Saturday afternoons at the park walking his dog, Waffles. It had amazed him the responsibility that come with being a dog owner- a responsibility that had been dropped in his lap two years ago when his brother had given him the dog as a birthday gift despite Castiel’s protest. Still, it was the responsibility towards his pet that had kept him out of his apartment most days. He had grown use to having to stop when random strangers came up to see if they could pet his dog. For some reason Waffles had particularly attracted the attention of small children, often children with parents who gave him suspicious look when they came to collect their offspring. Still, it had surprised him when a determined-looking toddler had appeared out of nowhere and had begun babbling to Waffles with little concern to the owner. It was also surprising that the girl’s parent hadn’t come running up like many others tended to do. He let out a little cough to catch the girl’s attention. She looks up, her eyes wide as saucers when she sees Castiel looking down at her. Still, she continues petting the dachshund with a fierce determination on her face. 

“Where are your parents?” he asks, trying to sound as stern as he gave the appearance of being. 

“My daddy is over there,” she says pointing to a figure on the park bench that overlooked the pond. It looked to be the same one as the one he and Dean had spent the entire night on, talking until the sun had risen the next day. The figure rises quickly and begins hurrying over to Castiel’s direction. 

“Hi, sorry, she does that sometime…” The man’s pace slows to a stop as he comes closer to Castiel. Dean Winchester stands before him, looking slightly stunned and mostly embarrassed. 

“Dean-” 

“I’m sorry, I didn’t mean to lose track of her. I just looked away for a second and she was gone,” Dean bumbles out. “Come on, Emma, we should leave the nice man alone.” 

The girl, _Emma_ , ignores her father for the attention of Waffles. Dean lets out a frustrated huff and looks as if he’s about to snap. 

“It’s fine,” Castiel reassures Dean. “I’m use to the attention that Waffles tracks.” 

Dean lets out a snort. “I still can’t believe you named your dog Waffles.”

“As a said before, it was my brother who insisted on the name.” 

They stand for a moment watching the toddler and the dog, before Dean clears his throat. 

“Cas, I know I’ve said this before, but I’m really sorry for ignoring you. If you would just let me explain.” 

“Dean, it seemed pretty clear to me what your feelings were towards me when you started ignoring me.”

“Damn it Cas, I thought you were dating my brother! And I was jealous!”

Although it doesn’t totally excuse Dean’s previous behaviour, this declaration certainly does explain it. It also makes Castiel feel a lot better about himself since he now knows that it wasn’t a fault of his that caused this problem. 

“Oh,” he states. “So your avoidance wasn’t because you took a dislike to me?” 

“No, dude,” Dean laughs. “I thought you were banging my brother. He kept going on about how serious he was this person and how he wanted to leave Jess for them. I thought he was talking about you and I was… I was beginning to develop, um… feelings towards you.” 

Oh… oh. 

“When you say feelings, what exactly do you mean?” 

Dean is turning red. Sam had warned that Dean wasn’t good with “emotional” stuff and Castiel could see how uncomfortable this conversation was making him.

“God, I don’t want to say love because that makes me sound like a sixteen year old girl, but if I had to put a name to these feelings, I guess _I’m sort of in love_ with you is the closest I could get,” Dean mumbles, looking at his feet as he says this. The cocky older brother that Sam had so often described is completely gone. 

“Do you often ignore the people you are in love with?” Castiel deadpans. Dean looks up, revealing a sheepish grin. 

“Has Sammy mentioned that I’m emotionally an eight-year old?” 

“No, but he did say you had the emotional range of a teaspoon.” Dean chuckles at that. “So you ignored me because you were afraid of getting hurt?” 

“Yeah,” Dean says, looking relieved. 

“But you never thought ahead enough to see that I would be hurt by you ignoring me?” 

“I know, I know. It was dick move. I’m really sorry. If there’s anything I could do to make it up to you.” 

“Well you could start by properly asking me out on a date… since you are so in love with me.” 

“What do you want me to get on my knees?” Dean jests. 

“Not until after dinner.” 

He expects a laugh from Dean for that, but instead Dean lunges forward, grabbing Castiel by the shoulders and pulls him to a kiss. At first, it’s awkward- their noses bump and Castiel is so in shock that he stands there stiff, unyielding. Dean steps back, looking disappointed and embarrassed. Dean rubs the back of his neck, the blush becoming deeper on his face. He looks like he’s about to leave, so Castiel steps forward. 

“I need more warning before you do something like that,” Cas stammers. He in turn, draws Dean closer to him and reaches over to cup Dean’s jaw. “Like this,” he says slowly, before pressing his lips to Dean’s. Quickly, he deepens the kiss. A low moan comes from Dean, which makes Castiel smirk. Dean is the first to break the kiss, quickly stepping back. 

“Um…” Castiel says. Dean points to the ground where Emma is still sitting, absentmindedly petting the dog, her attention on her father and Castiel, her eyes wide. “Oh, right. Maybe we should continue this another time.”

“I’ll hold you to it,” Dean says with a wide grin. Castiel watches as Dean gathers his daughter into his arms, and gives Castiel another one of those shit-eating grins that Dean seems to do. 

“So, I’ll text you later… or call… whatever,” Dean tells Castiel before they say goodbye. Castiel watches Dean and Emma as they leave, still a little stunned from the day’s events. 

“I certainly did not anticipate that when I decided to take you for a walk,” Castiel tells Waffles.

**Notes for the Chapter:**

> Well folks, this is all I have written so this might be the last update for a while because a) I'm a slow writer, and b) I'm not sure quite sure where to go next. Thanks for the comments and the kudos and hopefully I'll have more up soon!


End file.
